Reuters/Max Rossi
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James Middleton, 29, is the younger brother of Pippa and Kate, Duchess of Cambridge.
After dropping out of college, he picked up a reputation for reckless partying.
Later, he started a cake business that ultimately failed.
Now, he runs a custom marshmallow company - and seems to be settling down in a relationship.
Everyone knows Kate Middleton because of her dreamy royal wedding to Prince William. And everyone knows her younger sister, Pippa, because of the scene-stealing bridesmaid dress she wore to that wedding.
But fewer people know about the youngest Middleton: 29-year-old James, who's making his way in the business world as the head of a 100% serious, personalized marshmallow company called Boomf.
Here's a look at James's life both before and after his family became quasi-royalty.